38484-55-8

Basic information

• Product Name: (2S,5R)-2,5-Hexanediol
• Synonyms: (2R,5S)-2,5-Hexanediol;(2S,5R)-2,5-Hexanediol;(2S,5R)-Hexane-2,5-diol;meso-2,5-Hexanediol
• CAS NO: 38484-55-8
• Molecular Formula: C₆H₁₄O₂
• Molecular Weight: 0
• Mol File: 38484-55-8.mol
• Article Data: 8

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (2S,5R)-2,5-Hexanediol(CAS DataBase Reference)
• NIST Chemistry Reference: (2S,5R)-2,5-Hexanediol(38484-55-8)
• EPA Substance Registry System: (2S,5R)-2,5-Hexanediol(38484-55-8)

Safety Data

• Hazardous Substances Data: 38484-55-8(Hazardous Substances Data)

Upstream product

• 18545-25-0 5-methyl-tetrahydro-furan-2-ol 
• 18006-13-8 methyltriisopropoxytitanium(IV) 
• 5194-50-3 (E,Z)-2,4-hexadiene 
• 110-13-4 2,5-hexanedione 
• 3031-66-1 3-hexyn-2,5-diol 

Downstream Products

• 17397-24-9 hex-5-en-2-ol 
• 33447-90-4 meso-2,5-hexanediol dimethanesulfonate 
• 65709-73-1 (5R)-hydroxyhexane-2-one 

Relevant articles and documents

Biocatalytical production of (5S)-hydroxy-2-hexanone

Biocatalytical approaches have been investigated in order to improve accessibility of the bifunctional chiral building block (5S)-hydroxy-2-hexanone ((S)-2). As a result, a new synthetic route starting from 2,5-hexanedione (1) was developed for (S)-2, whi

Oxazaborolidine-catalysed reduction of alk-2-ene-1,4-diones. A convenient access to chiral 1,4-diols

An efficient method for the preparation of C2-symmetric, chiral alk-2- ene-1,4-diols (4) has been achieved, based on the borane-mediated reduction of symmetric alk-2-ene-1,4-diones (2) in the presence of oxazaborolidine (R)- 1. In general, the presence of the double bond in 2 has been beneficial (compared with the related saturated 1,4-diketones 3) not only as far as the stereoselectivity in the reduction step is concerned, but also because it allowed us to remove meso-4 by chomatography and/or to improve the stereochemical purity of several resulting mixtures of diols 4 by Sharpless' epoxidation. Enantioenricbed compounds 4 have been readily reduced to saturated diols with negligible loss of optical purity.

Yeast-mediated synthesis of optically active diols with C2-symmetry and (R)-4-pentanolide

Reduction of some diketones and a keteacid with yeast, Pichia farinosa IAM 4682 was examined. The reduction of carbonyl groups proceeded highly selectively with an anti-Prelog fashion to give (R)-alcohols. (2R,5R)2,5- Hexanediol (83% yd., >99% e.e., 95% d.e.), (2R,4R)-2,4-pentanediol (94% yd., >99% e.e., 98% d.e.), and (R)-4-pentanolide (67% yd., >99% e.e.) were highly efficiently obtained from the corresponding ketones. Effect of the structure of substrate on the stereochemical course as well as the selectivity were discussed.